Potassium Carbonate → HCID 71238620, compound

HRID 1846628Notes

Reaction equation

HRID 1846628 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](Cl)=[N:6][CH:7]=1.[C:12]([O:16][C:17](=[O:26])[NH:18][CH2:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)([CH3:15])([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[C:12]([O:16][C:17](=[O:26])[NH:18][CH2:19][CH:20]1[CH2:21][CH2:22][N:23]([C:5]2[C:4]([N+:9]([O-:11])=[O:10])=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)[CH2:24][CH2:25]1)([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamateHCID 70194125-Bromo-2-chloro-3-nitropyridine

Product 1

HCID 71238620HCID 71238620, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 1.00 g (4.21 mmol) 5-bromo-2-chloro-3-nitro-pyridine, 0.993 g (4.63 mmol) of piperidin-4-ylmethyl-carbamic acid tert-butyl ester, and 1.16 g (8.42 mmol) of potassium carbonate in N,N-dimethylformamide (10 mL) is stirred for 2 hours under argon. The mixture is diluted with water which causes a solid to precipitate from solution. The formed solid is collected by filtration, washed with water, and dried for 1 hour under vacuum at 50° C. to give 1.57 g (90.0%) of (5′-bromo-3′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-ylmethyl)-carbamic acid tert-butyl ester as a yellow solid.

Workup

  1. customto precipitate from solution
  2. filtrationThe formed solid is collected by filtration
  3. washwashed with water
  4. customdried for 1 hour under vacuum at 50° C.

Sources & evidence

ORD record
ord-55c1188379b647cf8a22ee4aea1777d1
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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